Category: 138775-03-8

Category: iodides-buliding-blocks. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid, is researched, Molecular C18H24N2O6, CAS is 138775-03-8, about Synthesis of N,N’-Orthogonally Protected (S)-Piperazine-2-carboxylic Acid. Author is Warshawsky, Alan M.; Patel, Meena V.; Chen, Teng-Man.

(S)-1-tert-butoxycarbonyl-4-benzyloxycarbonyl-2-piperazinecarboxylic acid was prepared in 4 steps and 40% overall yield from N-tert-butoxycarbonyl-L-serine β-lactone. The sequence required only a single chromatog. purification and yielded optically pure product.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, U.S. Gov’t, Non-P.H.S., Research Support, U.S. Gov’t, P.H.S., Journal of the American Chemical Society called Asymmetric Synthesis of Chiral Organofluorine Compounds: Use of Nonracemic Fluoroiodoacetic Acid as a Practical Electrophile and Its Application to the Synthesis of Monofluoro Hydroxyethylene Dipeptide Isosteres within a Novel Series of HIV Protease Inhibitors, Author is Myers, Andrew G.; Barbay, Joseph K.; Zhong, Boyu, which mentions a compound: 138775-03-8, SMILESS is O=C(N1[C@H](C(O)=O)CN(C(OCC2=CC=CC=C2)=O)CC1)OC(C)(C)C, Molecular C18H24N2O6, Application of 138775-03-8.

Two stereoselective routes to a series of diastereomeric inhibitors of HIV protease, monofluorinated analogs of the Merck HIV protease inhibitor indinavir, are described. The two routes feature stereoselective construction of the fluorinated core subunits by asym. alkylation reactions. The first-generation syntheses were based on the conjugate addition of the lithium enolate derived from pseudoephedrine α-fluoroacetamide to trans-nitroalkene Ph-CH2-CH:CH-NO2, a modestly diastereoselective transformation. A more practical second-generation synthetic route was developed that is based on a novel method for the asym. synthesis of organofluorine compounds, by enolate alkylation using optically active fluoroiodoacetic acid as the electrophile in combination with a chiral amide enolate. Resolution of fluoroiodoacetic acid with ephedrine provides either enantiomeric form of the electrophile in ≥96% ee. Alkylation reactions with this stable and storable chiral fluorinated precursor are shown to proceed in a highly stereospecific manner. With the development of substrate-controlled syn- or anti-selective reductions of α-fluoro ketones (I; F, CH2Ph trans and I; F, CH2Ph = cis; diastereomeric ratios 12:1-84:1), efficient and stereoselective routes to each of the four targeted inhibitors were achieved. The optimized synthetic route to the most potent inhibitor (II; Ki = 2.0 nM) proceeded in seven steps (87% average yield per step) from aminoindanol hydrocinnamide and (S)-fluoroiodoacetic acid, and allowed for the preparation of more than 1 g of this compound The inhibition of HIV-1 protease by each of the fluorinated inhibitors was evaluated in vitro, and the variation of potency as a function of inhibitor stereochem. is discussed.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Discovery of (2S)-N-[(1R)-2-[4-cyclohexyl-4-[[(1,1-dimethylethyl)amino]carbonyl]-1-piperidinyl]-1-[(4-fluorophenyl)methyl]-2-oxoethyl]-4-methyl-2-piperazinecarboxamide (MB243), a potent and selective melanocortin subtype-4 receptor agonist, published in 2005-01-03, which mentions a compound: 138775-03-8, mainly applied to piperazinecarboxamide preparation melanocortin receptor agonist structure, Formula: C18H24N2O6.

We report the discovery and optimization of substituted 2-piperazinecarboxamides as potent and selective agonists of the melanocortin subtype-4 receptor. Further in vivo development of lead agonist, MB243, is disclosed.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Synthesis of Enantiopure Piperazines via Asymmetric Lithiation-Trapping of N-Boc Piperazines: Unexpected Role of the Electrophile and Distal N-Substituent, published in 2016-01-20, which mentions a compound: 138775-03-8, mainly applied to synthesis enantiopure piperazine; asym lithiation piperazine, SDS of cas: 138775-03-8.

A new method for the synthesis of enantiopure α-substituted piperazines via direct functionalization of the intact piperazine ring is described. The approach utilizes the asym. lithiation-substitution of an α-methylbenzyl-functionalized N-Boc piperazine using s-BuLi/(-)-sparteine or (+)-sparteine surrogate and provides access to a range of piperazines (as single stereoisomers). Optimization of the new methodol. required a detailed mechanistic study. Surprisingly, it was found that the main culprits affecting the yield and enantioselectivity were the electrophile (the last reagent to be added to the reaction flask) and the distal N-substituent. The mechanistic studies included optimization of lithiation times using in situ IR spectroscopy, identification of a ring-fragmentation of the lithiated piperazines (that could be minimized with sterically hindered N-alkyl groups), and use of a novel “”diamine switch”” strategy to improve enantioselectivity with certain electrophiles. The methodol. was showcased with the preparation of an intermediate for Indinavir synthesis and the stereoselective synthesis of 2,5-trans- and 2,6-trans-piperazines.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid(SMILESS: O=C(N1[C@H](C(O)=O)CN(C(OCC2=CC=CC=C2)=O)CC1)OC(C)(C)C,cas:138775-03-8) is researched.SDS of cas: 75732-01-3. The article 《Identification of MK-5710 ((8aS)-8a-methyl-1,3-dioxo-2-[(1S,2R)-2-phenylcyclo- propyl]-N-(1-phenyl-1H-pyrazol-5-yl)hexahydro-imidazo[1,5-a]pyrazine-7(1H)-carboxamide), a potent smoothened antagonist for use in Hedgehog pathway dependent malignancies, Part 2》 in relation to this compound, is published in Bioorganic & Medicinal Chemistry Letters. Let’s take a look at the latest research on this compound (cas:138775-03-8).

The Hedgehog (Hh-) signaling pathway is a key developmental pathway which gets reactivated in many human tumors, and smoothened (Smo) antagonists are emerging as novel agents for the treatment of malignancies dependent on the Hh-pathway, with the most advanced compounds demonstrating encouraging results in initial clin. trials. A novel series of potent bicyclic hydantoin Smo antagonists was reported in the preceding article, these have been resolved, and optimized to identify potent homochiral derivatives with clean off-target profiles and good pharmacokinetic properties in preclin. species. While showing in vivo efficacy in mouse allograft models, unsubstituted bicyclic tetrahydroimidazo[1,5-a]pyrazine-1,3(2H,5H)-diones were shown to epimerize in plasma. Alkylation of the C-8 position blocks this epimerization, resulting in the identification of MK-5710 which was selected for further development.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Asymmetric Synthesis of Chiral Organofluorine Compounds: Use of Nonracemic Fluoroiodoacetic Acid as a Practical Electrophile and Its Application to the Synthesis of Monofluoro Hydroxyethylene Dipeptide Isosteres within a Novel Series of HIV Protease Inhibitors, published in 2001-08-01, which mentions a compound: 138775-03-8, mainly applied to fluoroacetamide nitroalkene diastereoselective conjugate addition preparation HIV1 protease inhibitor; asym alkylation fluoroiodoacetate amide enolate preparation HIV1 protease inhibitor; fluoro ketone preparation HIV1 protease inhibitor, Safety of (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid.

Two stereoselective routes to a series of diastereomeric inhibitors of HIV protease, monofluorinated analogs of the Merck HIV protease inhibitor indinavir, are described. The two routes feature stereoselective construction of the fluorinated core subunits by asym. alkylation reactions. The first-generation syntheses were based on the conjugate addition of the lithium enolate derived from pseudoephedrine α-fluoroacetamide to trans-nitroalkene Ph-CH2-CH:CH-NO2, a modestly diastereoselective transformation. A more practical second-generation synthetic route was developed that is based on a novel method for the asym. synthesis of organofluorine compounds, by enolate alkylation using optically active fluoroiodoacetic acid as the electrophile in combination with a chiral amide enolate. Resolution of fluoroiodoacetic acid with ephedrine provides either enantiomeric form of the electrophile in ≥96% ee. Alkylation reactions with this stable and storable chiral fluorinated precursor are shown to proceed in a highly stereospecific manner. With the development of substrate-controlled syn- or anti-selective reductions of α-fluoro ketones (I; F, CH2Ph trans and I; F, CH2Ph = cis; diastereomeric ratios 12:1-84:1), efficient and stereoselective routes to each of the four targeted inhibitors were achieved. The optimized synthetic route to the most potent inhibitor (II; Ki = 2.0 nM) proceeded in seven steps (87% average yield per step) from aminoindanol hydrocinnamide and (S)-fluoroiodoacetic acid, and allowed for the preparation of more than 1 g of this compound The inhibition of HIV-1 protease by each of the fluorinated inhibitors was evaluated in vitro, and the variation of potency as a function of inhibitor stereochem. is discussed.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Kinzel, Olaf; Alfieri, Anna; Altamura, Sergio; Brunetti, Mirko; Bufali, Simone; Colaceci, Fabrizio; Ferrigno, Federica; Filocamo, Gessica; Fonsi, Massimiliano; Gallinari, Paola; Malancona, Savina; Hernando, Jose Ignacio Martin; Monteagudo, Edith; Orsale, Maria Vittoria; Palumbi, Maria Cecilia; Pucci, Vincenzo; Rowley, Michael; Sasso, Romina; Scarpelli, Rita; Steinkuehler, Christian; Jones, Philip researched the compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid( cas:138775-03-8 ).Safety of (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid.They published the article 《Identification of MK-5710 ((8aS)-8a-methyl-1,3-dioxo-2-[(1S,2R)-2-phenylcyclo- propyl]-N-(1-phenyl-1H-pyrazol-5-yl)hexahydro-imidazo[1,5-a]pyrazine-7(1H)-carboxamide), a potent smoothened antagonist for use in Hedgehog pathway dependent malignancies, Part 2》 about this compound( cas:138775-03-8 ) in Bioorganic & Medicinal Chemistry Letters. Keywords: MK5710 preparation Hedgehog signaling smoothened antagonist antitumor pharmacokinetics. We’ll tell you more about this compound (cas:138775-03-8).

The Hedgehog (Hh-) signaling pathway is a key developmental pathway which gets reactivated in many human tumors, and smoothened (Smo) antagonists are emerging as novel agents for the treatment of malignancies dependent on the Hh-pathway, with the most advanced compounds demonstrating encouraging results in initial clin. trials. A novel series of potent bicyclic hydantoin Smo antagonists was reported in the preceding article, these have been resolved, and optimized to identify potent homochiral derivatives with clean off-target profiles and good pharmacokinetic properties in preclin. species. While showing in vivo efficacy in mouse allograft models, unsubstituted bicyclic tetrahydroimidazo[1,5-a]pyrazine-1,3(2H,5H)-diones were shown to epimerize in plasma. Alkylation of the C-8 position blocks this epimerization, resulting in the identification of MK-5710 which was selected for further development.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid(SMILESS: O=C(N1[C@H](C(O)=O)CN(C(OCC2=CC=CC=C2)=O)CC1)OC(C)(C)C,cas:138775-03-8) is researched.COA of Formula: C4H6N2O2S. The article 《Discovery of (2S)-N-[(1R)-2-[4-cyclohexyl-4-[[(1,1-dimethylethyl)amino]carbonyl]-1-piperidinyl]-1-[(4-fluorophenyl)methyl]-2-oxoethyl]-4-methyl-2-piperazinecarboxamide (MB243), a potent and selective melanocortin subtype-4 receptor agonist》 in relation to this compound, is published in Bioorganic & Medicinal Chemistry Letters. Let’s take a look at the latest research on this compound (cas:138775-03-8).

We report the discovery and optimization of substituted 2-piperazinecarboxamides as potent and selective agonists of the melanocortin subtype-4 receptor. Further in vivo development of lead agonist, MB243, is disclosed.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid, is researched, Molecular C18H24N2O6, CAS is 138775-03-8, about Synthesis of N,N’-Orthogonally Protected (S)-Piperazine-2-carboxylic Acid.HPLC of Formula: 138775-03-8.

(S)-1-tert-butoxycarbonyl-4-benzyloxycarbonyl-2-piperazinecarboxylic acid was prepared in 4 steps and 40% overall yield from N-tert-butoxycarbonyl-L-serine β-lactone. The sequence required only a single chromatog. purification and yielded optically pure product.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid, is researched, Molecular C18H24N2O6, CAS is 138775-03-8, about Identification of MK-5710 ((8aS)-8a-methyl-1,3-dioxo-2-[(1S,2R)-2-phenylcyclo- propyl]-N-(1-phenyl-1H-pyrazol-5-yl)hexahydro-imidazo[1,5-a]pyrazine-7(1H)-carboxamide), a potent smoothened antagonist for use in Hedgehog pathway dependent malignancies, Part 2, the main research direction is MK5710 preparation Hedgehog signaling smoothened antagonist antitumor pharmacokinetics.SDS of cas: 138775-03-8.

The Hedgehog (Hh-) signaling pathway is a key developmental pathway which gets reactivated in many human tumors, and smoothened (Smo) antagonists are emerging as novel agents for the treatment of malignancies dependent on the Hh-pathway, with the most advanced compounds demonstrating encouraging results in initial clin. trials. A novel series of potent bicyclic hydantoin Smo antagonists was reported in the preceding article, these have been resolved, and optimized to identify potent homochiral derivatives with clean off-target profiles and good pharmacokinetic properties in preclin. species. While showing in vivo efficacy in mouse allograft models, unsubstituted bicyclic tetrahydroimidazo[1,5-a]pyrazine-1,3(2H,5H)-diones were shown to epimerize in plasma. Alkylation of the C-8 position blocks this epimerization, resulting in the identification of MK-5710 which was selected for further development.

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